DE4017463A1 - Verfahren zur herstellung hochkonzentrierter pasten von alpha-sulfofettsaeure- alkylester-alkalimetallsalzen - Google Patents
Verfahren zur herstellung hochkonzentrierter pasten von alpha-sulfofettsaeure- alkylester-alkalimetallsalzenInfo
- Publication number
- DE4017463A1 DE4017463A1 DE4017463A DE4017463A DE4017463A1 DE 4017463 A1 DE4017463 A1 DE 4017463A1 DE 4017463 A DE4017463 A DE 4017463A DE 4017463 A DE4017463 A DE 4017463A DE 4017463 A1 DE4017463 A1 DE 4017463A1
- Authority
- DE
- Germany
- Prior art keywords
- weight
- sulfonation
- alkali metal
- ester
- aqueous
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 35
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000002253 acid Substances 0.000 claims description 45
- -1 alkyl ester alkali metal salts Chemical class 0.000 claims description 42
- 238000006386 neutralization reaction Methods 0.000 claims description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 27
- 239000000194 fatty acid Substances 0.000 claims description 27
- 229930195729 fatty acid Natural products 0.000 claims description 27
- 238000006277 sulfonation reaction Methods 0.000 claims description 27
- 239000008346 aqueous phase Substances 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 16
- 239000003599 detergent Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000004061 bleaching Methods 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000003925 fat Substances 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 239000007844 bleaching agent Substances 0.000 claims description 3
- 239000011552 falling film Substances 0.000 claims description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000009434 installation Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000019635 sulfation Effects 0.000 claims description 2
- 238000005670 sulfation reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 125000005907 alkyl ester group Chemical group 0.000 description 19
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000009897 hydrogen peroxide bleaching Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4017463A DE4017463A1 (de) | 1990-05-30 | 1990-05-30 | Verfahren zur herstellung hochkonzentrierter pasten von alpha-sulfofettsaeure- alkylester-alkalimetallsalzen |
| TR91/0442A TR25093A (tr) | 1990-05-30 | 1991-05-09 | ALFA-SüLFO YAG ASIDI ALKILESTER ALKALI METAL TUZLARINDAN COK KONSANTRE PASTALARIN üRETILMESINE MAHSUS USUL |
| MYPI91000824A MY107641A (en) | 1990-05-30 | 1991-05-16 | A process for the production of highly concentrated pastes of a-sulfofatty acid alkyl ester alkali metal salts. |
| PCT/EP1991/000942 WO1991018873A1 (fr) | 1990-05-30 | 1991-05-21 | PROCEDE DE PRODUCTION DE PATES TRES CONCENTREES DE SELS DE METAUX ALCALINS-ALKYLESTERS D'ACIDES GRAS α-SULFONIQUES |
| DE59106486T DE59106486D1 (de) | 1990-05-30 | 1991-05-21 | VERFAHREN ZUR HERSTELLUNG HOCHKONZENTRIERTER PASTEN VON -g(a)-SULFOFETTSÄUREALKYLESTER-ALKALIMETALLSALZEN. |
| EP91909738A EP0531355B1 (fr) | 1990-05-30 | 1991-05-21 | PROCEDE DE PRODUCTION DE PATES TRES CONCENTREES DE SELS DE METAUX ALCALINS-ALKYLESTERS D'ACIDES GRAS $g(a)-SULFONIQUES |
| US07/952,617 US5391782A (en) | 1990-05-30 | 1991-05-21 | Process for the production of highly concentrated pastes of α-sulfofatty acid alkyl ester alkali metal salts |
| JP3509187A JP2999554B2 (ja) | 1990-05-30 | 1991-05-21 | α―スルホ脂肪酸アルキルエステルアルカリ金属塩の高濃度ペーストの製法 |
| ES91909738T ES2076528T3 (es) | 1990-05-30 | 1991-05-21 | Procedimiento para la obtencion de pastas altamente concentradas de sales de metales alcalinos de esteres alquilicos de acidos alfa-sulfograsos. |
| CN91102790A CN1028364C (zh) | 1990-05-30 | 1991-05-29 | α-磺基脂肪酸烷基酯碱金属盐的高浓度糊剂的制备方法 |
| KR1019920703055A KR100200545B1 (ko) | 1990-05-30 | 1992-11-30 | 알파-술포지방산 알킬 에스테르 알칼리 금속 염의 고농축 페이스트의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4017463A DE4017463A1 (de) | 1990-05-30 | 1990-05-30 | Verfahren zur herstellung hochkonzentrierter pasten von alpha-sulfofettsaeure- alkylester-alkalimetallsalzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4017463A1 true DE4017463A1 (de) | 1991-12-05 |
Family
ID=6407507
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4017463A Withdrawn DE4017463A1 (de) | 1990-05-30 | 1990-05-30 | Verfahren zur herstellung hochkonzentrierter pasten von alpha-sulfofettsaeure- alkylester-alkalimetallsalzen |
| DE59106486T Expired - Fee Related DE59106486D1 (de) | 1990-05-30 | 1991-05-21 | VERFAHREN ZUR HERSTELLUNG HOCHKONZENTRIERTER PASTEN VON -g(a)-SULFOFETTSÄUREALKYLESTER-ALKALIMETALLSALZEN. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59106486T Expired - Fee Related DE59106486D1 (de) | 1990-05-30 | 1991-05-21 | VERFAHREN ZUR HERSTELLUNG HOCHKONZENTRIERTER PASTEN VON -g(a)-SULFOFETTSÄUREALKYLESTER-ALKALIMETALLSALZEN. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5391782A (fr) |
| EP (1) | EP0531355B1 (fr) |
| JP (1) | JP2999554B2 (fr) |
| KR (1) | KR100200545B1 (fr) |
| CN (1) | CN1028364C (fr) |
| DE (2) | DE4017463A1 (fr) |
| ES (1) | ES2076528T3 (fr) |
| MY (1) | MY107641A (fr) |
| TR (1) | TR25093A (fr) |
| WO (1) | WO1991018873A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4314885A1 (de) * | 1993-05-05 | 1994-11-10 | Sued Chemie Ag | Verfahren zur Neutralisation der Säureform von anionischen Tensiden, danach erhaltene Agglomerate und Waschmittel |
| US5688982A (en) * | 1993-08-20 | 1997-11-18 | The Procter & Gamble Company | No-bleach process for making sulfonated fatty acid alkyl ester surfactant |
| US6235913B1 (en) | 1997-08-05 | 2001-05-22 | Cognis Deutschland Gmbh | Method for producing fatty acid polyglycol ester sulphates |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY149706A (en) * | 2008-11-21 | 2013-09-30 | Lion Corp | Method for producing aqueous ?-sulfo fatty acid alkyl ester salt solution |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR844500A (fr) * | 1938-04-08 | 1939-07-26 | Savons Francais Soc D | Savon neutre ou acide en solution aqueuse et son mode de fabrication |
| BE546418A (fr) * | 1955-03-31 | |||
| DE1186051B (de) * | 1961-08-08 | 1965-01-28 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Sulfonierungserzeugnissen |
| BE716903A (fr) * | 1967-06-26 | 1968-12-02 | ||
| US3557006A (en) * | 1967-11-24 | 1971-01-19 | Peter J Ferrara | Composite toilet soap bar having an acid ph in use |
| US4396521A (en) * | 1976-04-22 | 1983-08-02 | Giuseppe Borrello | Solid detergent spotter |
| US4165293A (en) * | 1977-05-16 | 1979-08-21 | Amway Corporation | Solid transparent cleanser |
| JPS6036421B2 (ja) * | 1980-06-16 | 1985-08-20 | ライオン株式会社 | α−スルホ脂肪酸エステル塩の高濃度溶液の製法 |
| JPS5974195A (ja) * | 1982-09-30 | 1984-04-26 | ライオン株式会社 | α−スルホ脂肪酸エステル塩高濃度含有スラリ− |
| DE3305430A1 (de) * | 1983-02-17 | 1984-08-23 | Henkel KGaA, 4000 Düsseldorf | Verwendung von alkoholen und deren derivaten als viskositaetsregler fuer hochviskose technische tensid-konzentrate |
| DE3432324A1 (de) * | 1984-09-03 | 1986-03-13 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur regelung des disalzgehalts in (alpha)-sulfofettsaeureester-tensiden |
| DE3439520A1 (de) * | 1984-10-29 | 1986-04-30 | Henkel KGaA, 4000 Düsseldorf | Pumpfaehige hochkonzentrierte waessrige pasten vor alkalisalzen alpha-sulfonierter fettsaeurealkylester und verfahren zu ihrer herstellung |
| DE3538910A1 (de) * | 1985-11-02 | 1987-05-14 | Henkel Kgaa | Verfahren zur herstellung beweglicher pasten waschaktiver alpha-sulfofettsaeureestersalze hohen feststoffgehalts |
| EP0239165A3 (fr) * | 1986-03-27 | 1988-03-23 | Cornelis Van Buuren | Savon synthétique et son procédé de préparation |
| FI932366A0 (fi) * | 1990-11-26 | 1993-05-25 | Procter & Gamble | Format fastaemne, som aer gjort medelst anvaendning av ett styvt hopkopplat naet av en neutraliserad karboxylsyra |
-
1990
- 1990-05-30 DE DE4017463A patent/DE4017463A1/de not_active Withdrawn
-
1991
- 1991-05-09 TR TR91/0442A patent/TR25093A/xx unknown
- 1991-05-16 MY MYPI91000824A patent/MY107641A/en unknown
- 1991-05-21 US US07/952,617 patent/US5391782A/en not_active Expired - Fee Related
- 1991-05-21 ES ES91909738T patent/ES2076528T3/es not_active Expired - Lifetime
- 1991-05-21 EP EP91909738A patent/EP0531355B1/fr not_active Expired - Lifetime
- 1991-05-21 WO PCT/EP1991/000942 patent/WO1991018873A1/fr not_active Ceased
- 1991-05-21 JP JP3509187A patent/JP2999554B2/ja not_active Expired - Fee Related
- 1991-05-21 DE DE59106486T patent/DE59106486D1/de not_active Expired - Fee Related
- 1991-05-29 CN CN91102790A patent/CN1028364C/zh not_active Expired - Fee Related
-
1992
- 1992-11-30 KR KR1019920703055A patent/KR100200545B1/ko not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4314885A1 (de) * | 1993-05-05 | 1994-11-10 | Sued Chemie Ag | Verfahren zur Neutralisation der Säureform von anionischen Tensiden, danach erhaltene Agglomerate und Waschmittel |
| US5688982A (en) * | 1993-08-20 | 1997-11-18 | The Procter & Gamble Company | No-bleach process for making sulfonated fatty acid alkyl ester surfactant |
| US6235913B1 (en) | 1997-08-05 | 2001-05-22 | Cognis Deutschland Gmbh | Method for producing fatty acid polyglycol ester sulphates |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100200545B1 (ko) | 1999-06-15 |
| ES2076528T3 (es) | 1995-11-01 |
| JPH05506439A (ja) | 1993-09-22 |
| KR930700427A (ko) | 1993-03-15 |
| CN1056870A (zh) | 1991-12-11 |
| WO1991018873A1 (fr) | 1991-12-12 |
| TR25093A (tr) | 1992-11-01 |
| JP2999554B2 (ja) | 2000-01-17 |
| US5391782A (en) | 1995-02-21 |
| EP0531355B1 (fr) | 1995-09-13 |
| CN1028364C (zh) | 1995-05-10 |
| EP0531355A1 (fr) | 1993-03-17 |
| MY107641A (en) | 1996-05-30 |
| DE59106486D1 (de) | 1995-10-19 |
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